Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled
Cancel Clear Filters Apply Filters
More Filters

Price Per Night

$ $

Bedrooms

Bathrooms

Booking Options

Property Type

Location Type

Features

Managed By

Clear Filters
Use filters to narrow your search results!
Favorite
    Viewed 8 times in the last 48 hours
    Exceptional! 5/5
    (1 reviews)
    $50
    avg/night
    (7 nights min)
    House #112239ha
    1
    Favorite
      avg/night
      (7 nights min)
      Cottage #472272
      4
      Favorite
        Wonderful! 4.9/5
        (20 reviews)
        avg/night
        (3 nights min)
        House #223906
        20
        Favorite
          Viewed 10 times in the last 48 hours
          Wonderful! 4.9/5
          (13 reviews)
          avg/night
          (4 nights min)
          House #679747
          13
          Favorite
            Viewed 6 times in the last 48 hours
            Excellent! 4.7/5
            (15 reviews)
            avg/night
            (2 nights min)
            Estate #559364
            15
            Favorite
              Viewed 7 times in the last 48 hours
              Excellent! 4.7/5
              (12 reviews)
              avg/night
              (7 nights min)
              House #980094ha
              12
              Favorite
                Excellent! 4.6/5
                (5 reviews)
                avg/night
                (7 nights min)
                Cottage #580958
                5
                Favorite
                  Excellent! 4.6/5
                  (5 reviews)
                  avg/night
                  (7 nights min)
                  House #454191
                  5
                  Favorite
                    Exceptional! 5/5
                    (13 reviews)
                    avg/night
                    (3 - 7 nights min)
                    House #371811
                    13
                    Favorite
                      Viewed 5 times in the last 48 hours
                      Exceptional! 5/5
                      (6 reviews)
                      avg/night
                      (7 nights min)
                      House #340669
                      6
                      Favorite
                        Viewed 7 times in the last 48 hours
                        svg-lightning
                        avg/night
                        (2 nights min)
                        House #4506394ha
                        3
                        Favorite
                          Exceptional! 5/5
                          (9 reviews)
                          avg/night
                          (4 - 7 nights min)
                          House #3708573ha
                          9
                          Favorite
                            Viewed 8 times in the last 48 hours
                            Exceptional! 5/5
                            (16 reviews)
                            avg/night
                            (3 nights min)
                            House #174495
                            16
                            Favorite
                              Viewed 8 times in the last 48 hours
                              Wonderful! 4.9/5
                              (11 reviews)
                              avg/night
                              (7 nights min)
                              Cottage #165500ha
                              11
                              Favorite
                                avg/night
                                (5 nights min)
                                Cottage #3959151ha
                                1
                                Favorite
                                  Excellent! 4.5/5
                                  (11 reviews)
                                  avg/night
                                  (4 - 31 nights min)
                                  House #960479ha
                                  11
                                  Favorite
                                    Viewed 6 times in the last 48 hours
                                    Premier Partner
                                    Very Good! 4.1/5
                                    (7 reviews)
                                    svg-lightning
                                    avg/night
                                    Apartment #720739
                                    7
                                    Favorite
                                      Exceptional! 5/5
                                      (10 reviews)
                                      avg/night
                                      (7 nights min)
                                      House #131517ha
                                      10
                                      Favorite
                                        avg/night
                                        (7 nights min)
                                        Cottage #3779593ha
                                        2
                                        Favorite
                                          Viewed 8 times in the last 48 hours
                                          avg/night
                                          House #4746168ha
                                          Favorite
                                            Viewed 8 times in the last 48 hours
                                            avg/night
                                            (7 nights min)
                                            Cottage #4052295ha
                                            Favorite
                                              Exceptional! 5/5
                                              (11 reviews)
                                              avg/night
                                              (7 nights min)
                                              House #3932081ha
                                              11
                                              Favorite
                                                Viewed 10 times in the last 48 hours
                                                avg/night
                                                House #1011987
                                                4
                                                Favorite
                                                  Viewed 7 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (9 reviews)
                                                  avg/night
                                                  (2 - 7 nights min)
                                                  House #568907
                                                  9
                                                  Favorite
                                                    avg/night
                                                    (3 - 7 nights min)
                                                    House #4466657ha
                                                    1
                                                    Favorite
                                                      avg/night
                                                      (3 nights min)
                                                      House #182266ha
                                                      3
                                                      Favorite
                                                        Excellent! 4.7/5
                                                        (13 reviews)
                                                        avg/night
                                                        (4 nights min)
                                                        House #111340ha
                                                        13
                                                        Favorite
                                                          avg/night
                                                          (7 nights min)
                                                          House #119314ha
                                                          Favorite
                                                            Viewed 6 times in the last 48 hours
                                                            Exceptional! 5/5
                                                            (6 reviews)
                                                            avg/night
                                                            (7 nights min)
                                                            House #956719ha
                                                            6
                                                            Favorite
                                                              avg/night
                                                              (7 nights min)
                                                              House #859100
                                                              3
                                                              Favorite
                                                                Exceptional! 5/5
                                                                (10 reviews)
                                                                avg/night
                                                                (3 - 7 nights min)
                                                                House #704051
                                                                10
                                                                Favorite
                                                                  Viewed 10 times in the last 48 hours
                                                                  Premier Partner
                                                                  Exceptional! 5/5
                                                                  (5 reviews)
                                                                  svg-lightning
                                                                  avg/night
                                                                  House #883157
                                                                  5
                                                                  Favorite
                                                                    avg/night
                                                                    (2 - 3 nights min)
                                                                    House #1033086
                                                                    2
                                                                    Favorite
                                                                      Viewed 6 times in the last 48 hours
                                                                      avg/night
                                                                      (5 nights min)
                                                                      Cottage #1101741
                                                                      Favorite
                                                                        Viewed 8 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (11 reviews)
                                                                        avg/night
                                                                        (7 nights min)
                                                                        House #505692
                                                                        11
                                                                        Favorite
                                                                          Viewed 8 times in the last 48 hours
                                                                          avg/night
                                                                          (7 nights min)
                                                                          House #1101066
                                                                          Favorite
                                                                            svg-lightning
                                                                            avg/night
                                                                            House #1220493
                                                                            Favorite
                                                                              avg/night
                                                                              (14 nights min)
                                                                              House #715165
                                                                              3
                                                                              Favorite
                                                                                Excellent! 4.7/5
                                                                                (6 reviews)
                                                                                avg/night
                                                                                (3 nights min)
                                                                                House #3813604ha
                                                                                6
                                                                                Favorite
                                                                                  Exceptional! 5/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  (4 - 7 nights min)
                                                                                  House #837823
                                                                                  9
                                                                                  Favorite
                                                                                    Wonderful! 4.8/5
                                                                                    (6 reviews)
                                                                                    avg/night
                                                                                    (7 nights min)
                                                                                    House #3549672ha
                                                                                    6
                                                                                    Favorite
                                                                                      Viewed 6 times in the last 48 hours
                                                                                      avg/night
                                                                                      (3 nights min)
                                                                                      House #41681
                                                                                      2
                                                                                      Favorite
                                                                                        avg/night
                                                                                        (7 nights min)
                                                                                        Cottage #874121
                                                                                        3
                                                                                        Favorite
                                                                                          Exceptional! 5/5
                                                                                          (1 reviews)
                                                                                          avg/night
                                                                                          (7 nights min)
                                                                                          House #415177
                                                                                          1
                                                                                          Favorite
                                                                                            Exceptional! 5/5
                                                                                            (12 reviews)
                                                                                            avg/night
                                                                                            (7 nights min)
                                                                                            House #283441
                                                                                            12
                                                                                            Favorite
                                                                                              Viewed 7 times in the last 48 hours
                                                                                              Exceptional! 5/5
                                                                                              (7 reviews)
                                                                                              avg/night
                                                                                              (7 nights min)
                                                                                              House #216987
                                                                                              7
                                                                                              Favorite
                                                                                                avg/night
                                                                                                (7 nights min)
                                                                                                House #875840
                                                                                                Favorite
                                                                                                  avg/night
                                                                                                  (13 nights min)
                                                                                                  House #1052728
                                                                                                  2
                                                                                                  Favorite
                                                                                                    avg/night
                                                                                                    (7 nights min)
                                                                                                    House #240371ha
                                                                                                     

                                                                                                    Recent Chilmark Reviews

                                                                                                    Wonderful vacation retreat

                                                                                                    5 of 5
                                                                                                    Lovely comfortable home in a great location. Kitchen is well appointed for those who like to cook. Enjoy a quiet, relaxing space, spacious deck, and cozy comforts.
                                                                                                    • Submitted: Nov 30, 2017
                                                                                                    • Stayed: Nov 2017

                                                                                                    Weathering the Storm on Old County Road

                                                                                                    5 of 5
                                                                                                    I arrived at this lovely house in time for a visit from Jose...wind, rain, no sunshine, no boats to take my friends home. Very disappointing weather but that's how it goes sometimes. Staying in this house made it all bearable. The furnishings are comfortable but not fussy. The kitchen was well-stocked with utensils for those who really like to cook and it was pristine. The location is perfect if you love up-Island life. It was so quiet but not Spooky. The family that owns the house lives nearby and their daughter Colleen was such a gracious host. I hope to rent this home again next year.
                                                                                                    • Submitted: Sep 25, 2017
                                                                                                    • Stayed: Sep 2017